First rate comfort & style in the Second City

Staypineapple Chicago

Whether it’s a warm summer day or a teeth-chattering winter white-out, Staypineapple Chicago turns every visit into something special. If you’re wondering where to stay in Chicago, our historic downtown hotel offers the perfect balance of comfort and character. Each room and suite blends original architectural details with modern amenities such as HD TVs to stream your favorite shows, fast Wi-Fi to stay connected, and mini fridges to keep your drinks chilled and snacks close. 

Your perfect Chicago stay starts here.